538-08-9

Basic information

• Product Name: DIALLYL CYANAMIDE
• Synonyms: Cyanamide, di-2-propenyl-;Cyanamide, diallyl-;cyanamide,diallyl;di-2-propenyl-cyanamid;Di-2-propenylcyanamide;diallyl-cyanamid;Diallylkyanamid;DIALLYL CYANAMIDE
• CAS NO: 538-08-9
• Molecular Formula: C₇H₁₀N₂
• Molecular Weight: 122.17
• EINECS: 208-683-9
• Product Categories: monomer
• Mol File: 538-08-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: <-70 °C
• Boiling Point: bp90 140-145°; bp57 128-133°; bp18 105-110°
• Flash Point: 90.5°C
• Appearance: /
• Density: 0.9532 (rough estimate)
• Vapor Pressure: 0.0654mmHg at 25°C
• Refractive Index: 1.6230 (estimate)
• PKA: -6.76±0.70(Predicted)
• CAS DataBase Reference: DIALLYL CYANAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DIALLYL CYANAMIDE(538-08-9)
• EPA Substance Registry System: DIALLYL CYANAMIDE(538-08-9)

Safety Data

• Statements: 11-23/24/25-34
• Safety Statements: 9-16-26-36/37/39
• RIDADR: 3286
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 538-08-9(Hazardous Substances Data)

Usage

General Description

Diallyl cyanamide, also known as DAC, is a chemical compound with the molecular formula C6H10N2. It is a white crystalline solid that is highly soluble in organic solvents and slightly soluble in water. DAC is primarily used as a monomer in the production of thermosetting polymers, adhesives, and coatings due to its ability to undergo polymerization under heat and pressure. It is also used as a precursor for the synthesis of pharmaceuticals and agrochemicals. Diallyl cyanamide is classified as a potential carcinogen and is considered to have low acute toxicity, but prolonged exposure may cause skin and eye irritation. Therefore, proper safety measures should be taken when handling this chemical.

InChI:InChI=1/C7H10N2/c1-3-5-9(7-8)6-4-2/h3-4H,1-2,5-6H2

Upstream product

• 50-00-0 formaldehyd 
• 506-68-3 bromocyane 
• 106-95-6 allyl bromide 
• 100-46-9 benzylamine 
• 107-05-1 3-chloroprop-1-ene 
• 7677-24-9 trimethylsilyl cyanide 
• 124-02-7 diallylamine 
• 420-04-2 CYANAMID 
• 1469-70-1 allyl ethyl carbonate 
• 19981-17-0 sodium cyanamide 
• 20611-81-8 disodium cyanamide 

Downstream Products

• 124-02-7 diallylamine 
• 1531-36-8 dipropylamine-N-carbonitrile 
• 112033-08-6 N-allyl-N-propyl cyanamide 
• 93795-47-2 2-Diallylamino-6-p-tolyl-[1,3]oxazin-4-one 
• 93795-49-4 2-Diallylamino-6-(4-ethoxy-phenyl)-[1,3]oxazin-4-one 
• 93795-48-3 6-(4-Chloro-phenyl)-2-diallylamino-[1,3]oxazin-4-one 
• 6272-82-8 N,N-Diallyl-O-butyl-isoharnstoff 
• 89910-59-8 1,1-diallyl-thiourea 
• 91-77-0 diallylmelamine 
• 6280-33-7 5-diallylamino-tetrazole 

Relevant articles and documents

Electrochemical strategies for: N -cyanation of secondary amines and α C -cyanation of tertiary amines under transition metal-free conditions

Transition metal-free electrochemical approaches for the N-cyanation of secondary amines and the α C-cyanation of tertiary amines have been well established, with products being obtained in moderate to good yields and with good functional group tolerance under ambient conditions. The synthetic application of the protocols has been highlighted through scale-up experiments in a galvanostatic mode. Preliminary mechanistic investigation has confirmed that TBAB played a critical role in N-cyanation transformation and has indicated that the transformation might proceed via a free radical process. This journal is

N-Cyanation of Secondary Amines Using Trichloroacetonitrile

A one-pot N-cyanation of secondary amines has been developed using trichloroacetonitrile as an inexpensive cyano source. A diverse range of cyclic and acyclic secondary amines can be readily transformed into the corresponding cyanamides in good isolated yields, with the method successfully utilized in the final synthetic step of a biologically active rolipram-derived cyanamide. This approach exhibits distinct selectivity when compared to the use of highly toxic cyanogen bromide.

Phenyl chloro(thionoformate): A new dealkylating agent of tertiary amines

Phenyl chloro(thionoformate) reacts rapidly with unhindered tertiary aliphatic amines at 20° to give a thiocarbamate and an alkyl chloride. Dialkylcyclohexylamines react surprisingly rapidly to form predominantly cyclohexene. The thiocarbamates are converted into the secondary amine salt by treatment with dimethyl sulfate, followed by hydrolysis with water. Rates of reaction and alkyl group cleavage selectivity in amines were found to be superior or comparable to those previously reported with chloroformates.