31145-02-5

Basic information

• Product Name: CIS-4-DIMETHYLAMINOCINNAMONITRILE
• Synonyms: CIS-4-DIMETHYLAMINOCINNAMONITRILE
• CAS NO: 31145-02-5
• Molecular Formula: C₁₁H₁₂N₂
• Molecular Weight: 172.23
• EINECS: 932-851-7
• Mol File: 31145-02-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 58.0 to 62.0 °C
• Appearance: /
• CAS DataBase Reference: CIS-4-DIMETHYLAMINOCINNAMONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-4-DIMETHYLAMINOCINNAMONITRILE(31145-02-5)
• EPA Substance Registry System: CIS-4-DIMETHYLAMINOCINNAMONITRILE(31145-02-5)

Safety Data

• Hazardous Substances Data: 31145-02-5(Hazardous Substances Data)

Upstream product

• 100-10-7 4-dimethylamino-benzaldehyde 
• 75-05-8 acetonitrile 
• 97221-11-9 (E)-4-(((4-methoxyphenyl)imino)methyl)-N,N-dimethylaniline 
• 372-09-8 cyanoacetic acid 
• 3252-43-5 dibromoacetonitrile 
• 41463-93-8 4-N,N-dimethylaminobenzaldehyde hydrazone 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 7605-28-9 2-(phenylsulfonyl)acetonitrile 
• 141692-09-3 (E)-3-(4-(dimethylamino)phenyl)-2(phenylsulfonyl)acrylonitrile 
• 14378-09-7 2-Cyano-3-<4-(N,N-dimethylamino)phenyl>propenoic acid 

Relevant articles and documents

Optimization of chemical functionalities of indole-2-carboxamides to improve allosteric parameters for the cannabinoid receptor 1 (CB1)

5-Chloro-3-ethyl-N-(4-(piperidin-1-yl)phenethyl)-1H-indole-2-carboxamide (1; ORG27569) is a prototypical allosteric modulator for the cannabinoid type 1 receptor (CB1). Here, we reveal key structural requirements of indole-2-carboxamides for allosteric modulation of CB1: a critical chain length at the C3-position, an electron withdrawing group at the C5-position, the length of the linker between the amide bond and the phenyl ring B, and the amino substituent on the phenyl ring B these significantly impact the binding affinity (KB) and the binding cooperativity (α). A potent CB1 allosteric modulator 5-chloro-N-(4-(dimethylamino)phenethyl)-3-propyl-1H-indole- 2-carboxamide (12d) was identified. It exhibited a KB of 259.3 nM with a strikingly high binding α of 24.5. We also identified 5-chloro-N-(4-(dimethylamino)phenethyl)-3-hexyl-1H-indole-2-carboxamide (12f) with a KB of 89.1 nM, which is among the lowest KB values obtained for any allosteric modulator of CB1 these positive allosteric modulators of orthosteric agonist binding nonetheless antagonized the agonist-induced G-protein coupling to the CB1 receptor, yet induced β-arrestin mediated ERK1/2 phosphorylation.

A new method for the synthesis of cinnamonitriles by catalytic olefination

Catalytic olefination of hydrazones of aromatic aldehydes with dibromoacetonitrile affords cinnamonitriles.

STEREOSELECTIVE SYNTHESIS OF (2Z)-α,β-UNSATURATED NITRILES VIA TANDEM CONDENSATION-DESULFONYLATION OF α-CYANOSULFONES WITH ALDEHYDES

In the presence of sodium telluride, α-cyanosulfones undergo tandem condensation-desulfonylation reaction with aromatic aldehydes to give (2Z)-α,β-unsaturated nitriles with good stereoselectivity.