Structural formula
| Business number | 01T9 |
|---|---|
| Molecular formula | C13H10ClNO |
| Molecular weight | 231.68 |
| label |
Diphenylcarbamocarbon chloride, dimethylcarbamoyl chloride, N,N-Diphenylchloroformamide, diphenylcarbamide chloride, diphenylcarbamoyl chloride, Chloroformic acid diphenylamide, DPC-Cl |
Numbering system
CAS number:83-01-2
MDL number:MFCD00000633
EINECS number:201-450-2
RTECS number:EY5065000
BRN number:515312
PubChem number:24866819
Physical property data
1. Appearance: white powder
2. Density (g/mL, 25/4℃): Undetermined
3. Relative vapor density (g/mL, air =1): Uncertain
4. Melting point (ºC): 85
5. Boiling point (ºC, normal pressure): Uncertain
6. Boiling point (ºC, 5.2kPa): Uncertain
7. Refractive index: Uncertain
8. Flash point (ºC): Uncertain
9. Ratio Optical rotation (º): Uncertain
10. Autoignition point or ignition temperature (ºC): Uncertain
11. Vapor pressure (kPa, 25ºC): Uncertain
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12. Saturated vapor pressure (kPa, 60ºC): Uncertain
13. Heat of combustion (KJ/mol): Uncertain
14. Critical temperature (ºC ): Uncertain
15. Critical pressure (KPa): Uncertain
16. Log value of oil-water (octanol/water) partition coefficient: Uncertain
17. Upper explosion limit (%, V/V): Uncertain
18. Lower explosion limit (%, V/V): Uncertain
19. Solubility: Dissolved in most common solvents.
Toxicological data
None yet
Ecological data
None yet
Molecular structure data
1. Molar refractive index: 65.21
2. Molar volume (cm3/mol): 182.5
3. Isotonic specific volume (90.2K): 487.2
4. Surface tension (dyne/cm): 50.8
5. Polarizability (10-24cm3): 25.85
Compute chemical data
1. Hydrophobic parameter calculation reference value (XlogP): 3.8
2. Number of hydrogen bond donors: 0
3. Number of hydrogen bond acceptors: 1
4. Number of rotatable chemical bonds: 2
5. Topological molecular polar surface area (TPSA): 20.3
6. Number of heavy atoms: 16
7. Surface charge: 0
8. Complexity: 214
9. Number of isotope atoms: 0
10. Determine the number of atomic stereocenters : 0
11. Uncertain number of atomic stereocenters: 0
12. Determined number of chemical bond stereocenters: 0
13. Uncertain chemical bond formation Number of structural centers:0
14. Number of covalent bond units: 1
Properties and stability
It is hygroscopic and should be kept away from strong alkalis and strong oxidants; it is corrosive; unlike dimethylamino, diethylamino, and methylphenylcarbamoyl chloride, DPC-Cl does not have carcinogenic properties.
Storage method
Should be sealed and stored in a cool, dry place
Synthesis method
None yet
Purpose
1. Phenolic reagents. Organic Synthesis.
2. Diphenylcarbamoyl chloride (DPC-Cl) is a commonly used acylating reagent that can be used for Friedel-Crafts acylation; it can acylate amines, amino acids, thiols, phenols, and carboxylic acids Salt, etc.; can be used as a protective group during oligonucleotide synthesis, and the protective group can be removed under the action of concentrated ammonia-methanol or NaOH-methyl(ethanol) alcohol.
Introduction of carboxyl group Under the catalysis of AlCl3, DPC-Cl can introduce a carboxyl group on the aromatic ring. Alkyl or alkoxy substituted aromatic rings are susceptible to reaction. The product diphenylamide is hydrolyzed with alkali and then acidified to obtain carboxylic acid (formula 1)[1].
Reaction with amino groups DPC-Cl easily reacts with primary (formula 2) [2], secondary fatty amine (formula 3) [3] etc. [ 4~7].
Reaction with sulfhydryl group Under alkaline conditions (such as NaHCO3), DPC-Cl can react with thiols in ethanol solution (Formula 4)[8].
Used as oligomeric Protective groups during nucleotide synthesisWhen synthesizing oligonucleotides, the bases of guanine nucleosides are prone to side reactions and need to be protected. DPC-Cl can protect the enol isoforms of guanine bases. The conformation is protected by acylation. This method plays an important role in the synthesis of nucleoside compounds with guanine bases and those similar to guanine bases [9~12] ( Formula 5).
With double bonds Reaction of alcohol compounds DPC-Cl can undergo esterification reaction with alcohol compounds containing double bonds (Formula 6)[13].
With azide Reaction of sodium DPC-Cl can react with sodium azide to generate the corresponding azide compound (Formula 7)[14].
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Melted p-nitrotoluene (100%, 643.9kg ) carefully into the nitrification kettle (94.7kg of waste acid is placed in the kettle in advance, and the sulfuric acid content in the waste acid is about 77%. There is no waste acid in the first nitrification, and it can be replaced by sulfuric acid of considerable concentration), stir and cool down the temperature in the kettle to (55±2)℃ and then inject 316.2kg of mixed acid into a thin stream (mixed acid composition: 31.75% nitric acid, 64.85% sulfuric acid, 3.4% water. Dehydration value = 5). In the first stage, half of the mixed acid is added, and the feeding temperature is 52-56°C; in the second stage, half of the mixed acid is added, and the temperature gradually increases from 54°C to 70°C. After the mixed acid is added, the temperature is controlled at (70±2)°C. The time for adding mixed acid depends on the reaction temperature, usually about 6-7 hours. After the mixed acid is added, the temperature is raised to 75°C, kept warm and stirred for 2.25 hours, and the end point is measured. The freezing point reaches above 67°C as qualified. While stirring, carefully and slowly add 70L of cold water for dilution. Control the temperature at 75-77°C. Stir for 15 minutes after adding the water. Stop stirring and let stand for 0.5h, then insert the plastic tube to the bottom of the kettle and cool to room temperature. During the cooling process, please pay attention to condensation. When it is about to condense into a solid, be careful to continuously rotate the plastic tube and avoid muddying the liquid. Wait until all reactants solidify. Pull out the plastic tube, remove the spent acid, and heat to remelt the reactants. The temperature should not exceed 80°C. After melting, stop heating, stir for 3-5 minutes, let stand for 30 minutes, cool, and insert a plastic tube as above. After complete condensation, remove the plastic tube, drain out the waste acid, and reheat to melt. The temperature should not exceed 80°C. The reactant was a yellow oil and was kept at 75°C. Pour 1300L of water into the refining kettle, raise the temperature to 68-70°C, inject the yellow oil in a thin stream under stirring, add liquid caustic soda at any time for neutralization, and strictly control PH=5-6. Keep the temperature of the reactants at 67-68°C, spray cold water to cool down, and yellow needle-like crystals will appear. Continue to stir and cool to about 35°C, filter the material, and wash the filter cake with cold water to obtain yellow crystals of 2. 4-Dinitrotoluene. (2) Reduction 
Add 1300L of water to the reduction kettle, and add 500kg of iron powder under stirring. After heating to 70°C, add 40kg of 30% hydrochloric acid, raise the temperature to 90-95°C, take a sample and drop it on the filter paper. If black appears at the intersection of the wetting ring and 5% sulfide alkali solution, you can start adding dinitrogen in batches. Toluene (100% 364kg) makes the reaction proceed vigorously and maintains a boiling state of 100-102°C. When adding materials, check at any time. If a sample is dropped on the filter paper, there will be no yellow residue. The intersection with 5% sulfide alkali solution will appear black, and the intersection with litmus paper should appear red. After adding 75% of the total amount of dinitrotoluene, test the end point. Then add 100kg of iron powder with the same material in a cross-wise manner. The total feeding time is 1-1.5h, and always keep boiling. After adding the material, stir for another 0.5h. The end point is when the reaction solution wets the filter paper and does not show yellow. After the reduction end point is reached, stop heating and cool down to 85-90°C. Carefully add lime slurry made of 30kg of lime and water to make the pH value 8-9. Then add 5kg of 50% alkali sulfide and continue stirring for 15 minutes. The intersection of the wet circle on the filter paper and the 5% sulfide alkali solution without black traces is the end point of neutralization. After neutralization is completed, add 2kg of sodium sulfite, stir for 15 minutes, and let stand for 0.5h to allow the iron mud to fully precipitate. (3) Filtration, concentration and iron sludge sedimentationAfter that, suck the supernatant liquid into the storage tank, add 1000-1200L water to the iron sludge remaining in the reduction kettle, stir and raise the temperature to 95°C and let it stand for 0.5h, then suck the supernatant washing liquid into the storage tank, repeat the above method Wash three times, and the washing liquid is combined into the reduction mother liquor for suction filtration; after suction filtration, the material liquid is evaporated and concentrated under a vacuum of 80kg, which takes about 6 hours to complete. (4) Distillation under reduced pressure: Suction the concentrated liquid into the distillation kettle, and perform dehydration under stirring at a vacuum degree of 74.7-90.7kpa, an interlayer oil temperature of 180-210°C, and a top temperature of 50-60°C. When the vacuum degree rises to 94.7-97.3kpa, the top temperature is 190-200°C, and the interlayer oil temperature is 280-290°C for distillation. As the material in the distillation kettle decreases, the vacuum gradually rises, and the top temperature gradually drops to 170-180°C. ℃, the oil temperature increases to about 300-320 ℃, at which point the distillation can be considered to have reached the end. Each batch of finished products is about 500kg. Raw material consumption quota: p-nitrotoluene 1600kg/t, sulfuric acid (98%) 1616kg/t, nitric acid (98%) 760kg/t, iron powder (90%) 2700kg/t. 
