29091-21-2

Basic information

• Product Name: Prodiamine
• Synonyms: blockade;CN-11-2936;endurance;Marathon;m-Phenylenediamine, 2,4-dinitro-N3,N3-dipropyl-6-(trifluoromethyl)-;n(sup3),n(sup3)-dipropyl-2,4-dinitro-6-trifluoromethyl-m-phenylenediamine;N3,N3-Dipropyl-2,4-dinitro-6-trifluoromethyl-m-phenylenediamine;Toluene-2,4-diamine, alpha,alpha,alpha-trifluoro-3,5-dinitro-N4,N4-dipropyl-
• CAS NO: 29091-21-2
• Molecular Formula: C₁₃H₁₇F₃N₄O₄
• Molecular Weight: 350.29
• EINECS: 249-421-3
• Product Categories: Protective Apparel Fabric;PhenylenediamineAlphabetic;Alpha sort;DinitroanilinePesticides&Metabolites;Herbicides;N-PPesticides&Metabolites;P;Pesticides&Metabolites;PON - PT
• Mol File: 29091-21-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 124-125°
• Boiling Point: 433 °C at 760 mmHg
• Flash Point: -18 °C
• Appearance: ⁴⁸
• Density: 1.4700
• Storage Temp.: 0-6°C
• PKA: -1.40±0.50(Predicted)
• BRN: 2494213
• CAS DataBase Reference: Prodiamine(CAS DataBase Reference)
• NIST Chemistry Reference: Prodiamine(29091-21-2)
• EPA Substance Registry System: Prodiamine(29091-21-2)

Safety Data

• Hazard Codes: F;Xn;N,N,Xn,F
• Statements: 11-38-50/53-65-67-20
• Safety Statements: 60-61-62-33-25-16-9
• RIDADR: UN 1145
• WGK Germany: 2
• Hazardous Substances Data: 29091-21-2(Hazardous Substances Data)

Usage

Uses

Herbicide.

InChI:InChI=1/C13H17F3N4O4/c1-3-5-18(6-4-2)11-9(19(21)22)7-8(13(14,15)16)10(17)12(11)20(23)24/h7H,3-6,17H2,1-2H3

Synthetic route

2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + di-n-propylamine (142-84-7) → prodiamine (29091-21-2)

Conditions	Yield
(i) EtOH, (ii) NH3; Multistep reaction;

N,n-dipropyl-3-chloro-2,6-dinitro-4-trifluoromethylaniline (29091-20-1) → prodiamine (29091-21-2)

Conditions	Yield
With ammonia In 1,4-dioxane at 95 - 100℃; for 40h; Sealed flask;	0.345 g

Upstream product

• 29091-20-1 N,n-dipropyl-3-chloro-2,6-dinitro-4-trifluoromethylaniline 
• 29091-09-6 2,4-dichloro-3,5-dinitro-benzotrifluoride 
• 142-84-7 di-n-propylamine 

Relevant articles and documents

Synthesis and evaluation of oryzalin analogs against Toxoplasma gondii

The synthesis and evaluation of 20 dinitroanilines and related compounds against the obligate intracellular parasite Toxoplasma gondii is reported. Using in vitro cultures of parasites in human fibroblasts, we determined that most of these compounds selectively disrupted Toxoplasma microtubules, and several displayed sub-micromolar potency against the parasite. The most potent compound was N1,N1-dipropyl-2,6-dinitro-4-(trifluoromethyl)-1,3- benzenediamine (18b), which displayed an IC50 value of 36 nM against intracellular T. gondii. Based on these data and another recent report [Ma, C.; Tran, J.; Gu, F.; Ochoa, R.; Li, C.; Sept, D.; Werbovetz, K.; Morrissette, N. Antimicrob. Agents Chemother. 2010, 54, 1453], an antimitotic structure-activity relationship for dinitroanilines versus Toxoplasma is presented.

3-Halo-2,6-dinitro-4-trifluoromethylaniline

3-Halo-2,6-dinitro-4-trifluoromethylanilines having hydrocarbon substituents on the nitrogen atom. The hydrocarbon substituents can be alkyl, alkenyl, alkynyl or a portion of a heterocyclic group. The compounds are especially useful as intermediates for preparing herbicidal dinitro-1,3-phenylenediamines.