628-87-5

Basic information

• Product Name: Iminodiacetonitrile
• Synonyms: 1,1’-imidodiacetonitrile;1,1'-Imidodiacetonitrile;2,2’-iminobis-acetonitril;2,2’-iminobisacetonitrile;2406 I.S.;2406i.s.;Acetonitrile, 2,2'-iminobis-;Di(cianometil)ammina
• CAS NO: 628-87-5
• Molecular Formula: C₄H₅N₃
• Molecular Weight: 95.1
• EINECS: 211-058-3
• Product Categories: C1 to C5;Cyanides/Nitriles;Nitrogen Compounds
• Mol File: 628-87-5.mol
• Article Data: 19

Chemical Properties

• Melting Point: 69-71 °C(lit.)
• Boiling Point: 167.6°C (rough estimate)
• Flash Point: 157.9 °C
• Appearance: tan to dark brown crystalline powder, crystals
• Density: 1.1031 (rough estimate)
• Vapor Pressure: 0.000104mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: -1.25±0.20(Predicted)
• Water Solubility: Soluble in water, acetone and hot methanol.
• BRN: 773803
• CAS DataBase Reference: Iminodiacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: Iminodiacetonitrile(628-87-5)
• EPA Substance Registry System: Iminodiacetonitrile(628-87-5)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39-36/37
• WGK Germany: 3
• RTECS: AM0650000
• TSCA: Yes
• Hazardous Substances Data: 628-87-5(Hazardous Substances Data)

Usage

Chemical Properties

tan to dark brown crystalline powder, crystals

Uses

Iminodiacetonitrile is used as a chemical intermediate. It is also used in the preparation of iminodiacetic acid. Further, it is used to study the interference of nitriles in cyanide determination.

Definition

ChEBI: A secondary amino compound that is ammonia in which two of the hydrogens are substituted by cyanomethyl groups.

Synthesis Reference(s)

The Journal of Organic Chemistry, 21, p. 1211, 1956 DOI: 10.1021/jo01117a002

InChI:InChI=1/C4H5N3/c5-1-3-7-4-2-6/h7H,3-4H2/p+1

Synthetic route

1,3,5-tris(cyanomethyl)hexahydro-1,3,5-triazine (4560-87-6) + desaminomethylporphobilinogendinitrile (106491-24-1) → uroporphyrinogenoctanitrile + iminodiacetonitrile (628-87-5)

Conditions	Yield
With Montmorillonite K10 In acetonitrile at 180℃; for 0.5h;	A 80% B n/a

2,2′-iminobis(acetamide) (21954-96-1) → iminodiacetonitrile (628-87-5)

Conditions	Yield
With phosphorus pentoxide under 15.0015 - 37.5038 Torr; for 1h; Temperature; Heating;	79%
under 15.0015 - 37.5038 Torr; for 1h; Temperature; Heating;

2-aminopentanedinitrile (2478-50-4) + 2-aminoacetonitrile (540-61-4) → rac-N2-(Cyanmethyl)glutamindinitril (959051-09-3) + iminodiacetonitrile (628-87-5)

Conditions	Yield
at 80℃; for 16h; Yields of byproduct given;	A 75% B n/a

hydrogen cyanide (74-90-8) + methyleneaminoacetonitrile (109-82-0) → iminodiacetonitrile (628-87-5)

Conditions	Yield
With sulfuric acid In methanol at 60℃; for 3h;	52%
With hydrogenchloride

glycolonitrile (107-16-4) + 2-aminoacetonitrile (540-61-4) → iminodiacetonitrile (628-87-5)

Conditions	Yield
In ethanol reflux, 2.5 h; -20 deg C, 10 h;	30%
With phosphoric acid

2-cyanoaziridine (33898-53-2) → methyl isocyanate (593-75-9, 685498-28-6) + N-(methylimino)acetonitrile (59264-17-4) + acetonitrile (75-05-8) + iminodiacetonitrile (628-87-5)

Conditions	Yield
With 3 A molecular sieve at 370℃; under 0.1 Torr; Product distribution; flash vaccum pyrolysis at variation of temp.;	A 9.5% B 10.5% C 6% D n/a
With 3 A molecular sieve at 370℃; under 0.1 Torr;	A 9.5% B 10.5% C 6% D n/a

2-cyanoaziridine (33898-53-2) → butanedinitrile (110-61-2) + (E/Z)-3-aminoprop-2-enenitrile (19866-98-9) + iminodiacetonitrile (628-87-5)

Conditions	Yield
With quartz at 630℃; under 0.1 Torr; Product distribution; flash vaccum pyrolysis;	A 3% B 4.8% C 2%
With quartz at 630℃; under 0.1 Torr;	A 3% B 4.8% C 2%

formaldehyd (50-00-0) → iminodiacetonitrile (628-87-5)

Conditions	Yield
With ammonia; water beim folgenden Behandeln mit HCN und wss.HCl;

hydrogen cyanide (74-90-8) + hexamethylenetetramine (100-97-0) → iminodiacetonitrile (628-87-5)

hexamethylenetetramine (100-97-0) → iminodiacetonitrile (628-87-5)

Conditions	Yield
With hydrogen cyanide

chloroacetonitrile (107-14-2) → iminodiacetonitrile (628-87-5)

Conditions	Yield
With ammonia

glycolonitrile (107-16-4) → iminodiacetonitrile (628-87-5)

Conditions	Yield
With ammonia

hydrogen cyanide (74-90-8) + 2-aminoacetonitrile (540-61-4) → iminodiacetonitrile (628-87-5)

Conditions	Yield
In water at 25℃; Equilibrium constant; effect of pH;

chloroacetonitrile (107-14-2) + gaseous NH3 → iminodiacetonitrile (628-87-5)

2-aminoacetonitrile (540-61-4) → iminodiacetonitrile (628-87-5)

Conditions	Yield
With ammonia In water at 100℃; for 0.333333h; Product distribution / selectivity;

formaldehyd (50-00-0) + hydrogen cyanide (74-90-8) → iminodiacetonitrile (628-87-5)

Conditions	Yield
With hexamethylenetetramine; oxygen at 45℃; for 12h; Time; Temperature;

iminodiacetic acid hydrochloride + iminodiacetonitrile (628-87-5) → phosphonomethylimino-di-acetic acid (5994-61-6)

Conditions	Yield
Stage #1: iminodiacetonitrile With sodium hydroxide In water at 100 - 110℃; for 1h; Stage #2: iminodiacetic acid hydrochloride With dihydrogen peroxide; pyrographite at 80 - 100℃; for 0.5h; Stage #3: With formaldehyd; phosphoric acid at 110℃; for 3h; Reagent/catalyst;	98.5%

hydrogen cyanide (74-90-8) + acetaldehyde (75-07-0) + iminodiacetonitrile (628-87-5) → methylglycinenitrile-N,N-diacetonitrile (185257-07-2)

Conditions	Yield
With sulfuric acid In water at 60 - 80℃; for 2.25h; pH=1.2 - 1.8; Product distribution / selectivity;	98%
Stage #1: iminodiacetonitrile With sulfuric acid In water at 60℃; pH=1.8; Stage #2: hydrogen cyanide; acetaldehyde In water at 60 - 80℃; for 2.25h; pH=1.2;
With sulfuric acid In water at 60 - 80℃; for 2.25h; pH=~ 1.2 - 1.8;

iminodiacetonitrile (628-87-5) → piperazine (110-85-0) + 1,5-diamino-3-azapentane (111-40-0)

Conditions	Yield
With ammonia; hydrogen; potassium hydroxide In ethanol at 80℃; under 90009 Torr; Pressure; Reagent/catalyst; Solvent; Temperature; Time;	A 1.03% B 97.53%

iminodiacetonitrile (628-87-5) → iminodiacetic acid (142-73-4)

Conditions	Yield
With sodium hydroxide at 60 - 65℃; for 1h; Time;	97.25%
With water; calcium hydroxide at 25℃; for 5h;	90%
With Alcaligenes faecalis ZJUTBX11 cells encapsulated in alginate-chitosan-alginate membrane liquid core capsules In aq. buffer at 35℃; pH=7.5; Kinetics; Reagent/catalyst; pH-value; Enzymatic reaction;

Glutaraldehyde (111-30-8) + iminodiacetonitrile (628-87-5) → 1,2-propylenebis(D,L-glycinonitrile-N,N-diacetonitrile)

Conditions	Yield
With hydrogen isocyanide; sulfuric acid In hydrogen cyanide; water	97%

1,2-dichloro-ethane (107-06-2) + iminodiacetonitrile (628-87-5) → ethylenediaminetetraacetic acid (60-00-4)

Conditions	Yield
Stage #1: 1,2-dichloro-ethane; iminodiacetonitrile With calcium oxide In 5,5-dimethyl-1,3-cyclohexadiene at 105 - 115℃; for 9.5h; Large scale; Stage #2: With sodium hydroxide In water at 70 - 80℃; for 9h; Reagent/catalyst; Solvent; Temperature; Large scale;	96.83%

1-Bromo-2-chloroethane (107-04-0) + iminodiacetonitrile (628-87-5) → ethylenediaminetetraacetic acid (60-00-4)

Conditions	Yield
Stage #1: 1-Bromo-2-chloroethane; iminodiacetonitrile With calcium oxide In 5,5-dimethyl-1,3-cyclohexadiene at 105 - 115℃; for 9h; Stage #2: With sodium hydroxide In water at 70 - 80℃; for 8.5h;	95.47%

iminodiacetonitrile (628-87-5) → N-nitroso-bis(cyanomethyl)amine (16339-18-7)

Conditions	Yield
With sulfuric acid; sodium nitrite In water at 0 - 30℃; for 2.5h; Temperature;	95%
With sulfuric acid; sodium nitrite In water at 0 - 30℃; for 2.5h;	89%
With sulfuric acid; sodium nitrite

formaldehyd (50-00-0) + iminodiacetonitrile (628-87-5) → phosphonomethylimino-di-acetic acid (5994-61-6)

Conditions	Yield
Stage #1: iminodiacetonitrile With sodium hydroxide In water at 45 - 50℃; for 1h; Stage #2: With phosphorus trichloride Stage #3: formaldehyd at 115 - 120℃; for 2h;	93.8%
Stage #1: iminodiacetonitrile With hydrogenchloride; sulfuric acid In water at 80 - 160℃; under 1500.15 - 15001.5 Torr; for 6h; Inert atmosphere; Autoclave; Stage #2: formaldehyd With phosphonic Acid In water for 3h; Pressure; Temperature; Inert atmosphere; Autoclave; Reflux;	90.52%

benzoyl chloride (98-88-4) + iminodiacetonitrile (628-87-5) → N,N-bis(cyanomethyl)benzamide (36130-48-0)

Conditions	Yield
With pyridine; triethylamine at 0 - 20℃; for 4.33333h;	93%
With benzene at 110 - 120℃;
With pyridine
With benzene
With potassium carbonate In dichloromethane; water for 2h; Ambient temperature;

(2R)-2-{4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy}propanoyl chloride + iminodiacetonitrile (628-87-5) → (2R)-2-{4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy}-N,N-bis(cyanomethyl)propanamide

Conditions	Yield
With triethylamine In dichloromethane at 0 - 35℃;	92%

2-amino-benzenethiol (137-07-5) + iminodiacetonitrile (628-87-5) → bis(1,3-benzothiazol-2-ylmethyl)amine (854070-43-2)

Conditions	Yield
With quinoline In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; for 1h;	91%
In ethylene glycol Heating;

formaldehyd (50-00-0) + iminodiacetonitrile (628-87-5) → N-methyliminodiacetonitrile (5423-24-5)

Conditions	Yield
With hydrogenchloride In methanol; water at 20℃; for 1h; pH=2;	89.4%

trifluoroacetic anhydride (407-25-0) + iminodiacetonitrile (628-87-5) → N-(trifluoroacetyl)iminodiacetonitrile (1182284-06-5)

Conditions	Yield
In dichloromethane at 0 - 20℃; for 24.3333h;	89%

iminodiacetonitrile (628-87-5) → 2,2'-imino-bis-acetamide oxime (20004-00-6, 76412-51-6)

Conditions	Yield
With hydroxylamine In methanol; water at 20℃; for 48h;	88.7%
With hydroxylamine In methanol

iminodiacetonitrile (628-87-5) → 2,2'-azanediylbis(N'-hydroxyacetimidamide) (20004-00-6, 76412-51-6)

Conditions	Yield
With hydroxylamine In methanol; water	88.7%

valproyl chloride (2936-08-5) + iminodiacetonitrile (628-87-5) → 2-Propyl-pentanoic acid bis-cyanomethyl-amide (89508-09-8)

Conditions	Yield
With potassium carbonate In dichloromethane; water for 2h; Ambient temperature;	86%

cyclohexanylcarbonyl chloride (2719-27-9) + iminodiacetonitrile (628-87-5) → Cyclohexanecarboxylic acid bis-cyanomethyl-amide (87693-71-8)

Conditions	Yield
With potassium carbonate In dichloromethane; water for 2h; Ambient temperature;	85%
With potassium carbonate In dichloromethane; water for 2h; Ambient temperature;

iminodiacetonitrile (628-87-5) → bis(cyanomethyl)ammonium hexafluorophosphate

Conditions	Yield
Stage #1: iminodiacetonitrile With hydrogenchloride In methanol; water at 0℃; Stage #2: With silver(I) hexafluorophosphate In methanol; acetonitrile	81%

p-toluenesulfonyl chloride (98-59-9) + iminodiacetonitrile (628-87-5) → N,N-Bis-cyanomethyl-4-methyl-benzenesulfonamide (198954-96-0)

Conditions	Yield
With pyridine 1.) 0 deg C, 3 h, 2.) room temperature, 2 h;	78%

methanol (67-56-1) + iminodiacetonitrile (628-87-5) → 2-(Methoxycarbonimidoylmethyl-amino)-acetimidic acid methyl ester; hydrochloride

Conditions	Yield
With hydrogenchloride In diethyl ether at 0℃; Inert atmosphere;	76%
With hydrogenchloride

iminodiacetonitrile (628-87-5) → α-(cyanomethylamino)acetic acid + iminodiacetic acid (142-73-4)

Conditions	Yield
With Sphingomonas wittichii nitrilase NIT158; water In aq. phosphate buffer at 37℃; for 24h; pH=7.3; pH-value; Temperature; Solvent; Enzymatic reaction; enantiospecific reaction;	A 73% B n/a

1,3,5-trichloro-2,4,6-triazine (108-77-0) + iminodiacetonitrile (628-87-5) → 2,2'-[(4-{[2-(λ2-azanylidene)-2λ3-ethyl](cyanomethyl)amino}-6-chloro-1,3,5-triazin-2-yl)azanediyl]diacetonitrile (30682-50-9)

Conditions	Yield
With benzoyl chloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; for 20h; Inert atmosphere;	65%

Toluene-4-sulfonic acid 2-(5-methyl-2,4-dioxo-6-phenylsulfanyl-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-ethyl ester (189637-25-0) + iminodiacetonitrile (628-87-5) → {Cyanomethyl-[2-(5-methyl-2,4-dioxo-6-phenylsulfanyl-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-ethyl]-amino}-acetonitrile

Conditions	Yield
With pyridine for 24h;	58%

iminodiacetonitrile (628-87-5) → 2,2′-iminobis(acetamide) (21954-96-1)

Conditions	Yield
Stage #1: iminodiacetonitrile With hydrogenchloride In isopropyl alcohol at 50℃; for 15h; Stage #2: With ammonium hydroxide In water pH=10;	45%
With sulfuric acid; acetic acid

Upstream product

• 74-90-8 hydrogen cyanide 
• 109-82-0 methyleneaminoacetonitrile 
• 100-97-0 hexamethylenetetramine 
• 4560-87-6 1,3,5-tris(cyanomethyl)hexahydro-1,3,5-triazine 
• 106491-24-1 desaminomethylporphobilinogendinitrile 
• 75-07-0 acetaldehyde 
• 21954-96-1 2,2′-iminobis(acetamide) 
• 50-00-0 formaldehyd 
• 540-61-4 2-aminoacetonitrile 
• 107-14-2 chloroacetonitrile 
• 33898-53-2 2-cyanoaziridine 
• 2478-50-4 glutamic acid dinitrile 
• 107-16-4 glycolonitrile 

Downstream Products

• 16728-92-0 N-benzyl-N,N-bis(cyanomethyl)amine 
• 99988-97-3 phenyl-acetic acid-(bis-cyanomethyl-amide) 
• 7327-60-8 nitrilotriacetonitrile 
• 1116-43-4 methanediyldiimino-tetra-acetonitrile 
• 185257-07-2 methylglycinenitrile-N,N-diacetonitrile 
• 21821-06-7 [4-amino-3-(4-methoxy-phenyl)-2-oxo-2,3-dihydro-imidazol-1-yl]-acetonitrile 
• 5994-61-6 phosphonomethylimino-di-acetic acid 
• 110-85-0 piperazine 
• 111-40-0 3-azapentane-1,5-diamine 
• 41536-72-5 2,6-diamino-1λ⁵-pyrazin-1-one 
• 14257-15-9 2,2'-Imino-bis-(cyanacet-4-chloranilid) 
• 16339-18-7 N-nitroso-bis(cyanomethyl)amine 
• 6290-05-7 Diethyl iminodiacetate 
• 39987-25-2 dimethyl iminodiacetate hydrochloride 

Relevant articles and documents

Precursors of biological cofactors from ultraviolet irradiation of circumstellar/interstellar ice analogues

Biological cofactors include functionalized derivatives of cyclic tetrapyrrole structures that incorporate different metal ions. They build up structural partnerships with proteins, which play a crucial role in biochemical reactions. Porphyrin, chlorin, bacteriochlorin, and corrin are the basic structures of cofactors (heme. chlorophyll, bacteriochlorophyll, siroheme, F 430, and vitamin B12). Laboratory and theoretical work suggest that the molecular building blocks of proteins (α-amino acids) and nucleic acids (carbohydrates, purines, and pyrimidines) were generated under prebiotic conditions. On the other hand, experimental data on the prebiotic chemistry of cofactors are rare. We propose to search directly for the pathways of the formation of cofactors in the laboratory. Herein we report on the detection of N-heterocycles and amines in the room-temperature residue obtained after photo- and thermal processing of an interstellar ice analogue under high vacuum at 12 K. Among them, hexahydro-1,3,5-triazine and its derivatives, together with monopyrrolic molecules, are precursors of porphinoid cofactors. Hexahydropyrimidine was also detected. This is the first detection of these compounds in experiments simulating circumstellar/interstellar conditions. Except for 2-aminopyrrole and 2,4-diaminofuran, which were only found in 13C-labeled experiments, all the reported species were detected in both 12C- and 13C-labeled experiments, excluding contamination. The molecules reported here might be present in circumstellar/interstellar grains and cometary dust and could be detected by the Stardust and Rosetta missions.

Corresponding amine nitrile and method of manufacturing thereof (by machine translation)

The present invention relates to a nitrile manufacturing method, which has characteristics of significantly-reduced ammonia source consumption, low environmental pressure, low energy consumption, low production cost, high nitrile purity, high nitrile yield and the like compared with the method in the prior art, wherein nitrile having a complicated structure can be obtained through the method. The present invention further relates to a method for producing a corresponding amine from the nitrile.

Corresponding amine nitrile and method of manufacturing thereof

The invention relates to a preparation method of nitrile. Compared with the prior art, the preparation method has the characteristics of obvious reduction of the usage amount of ammonia sources, low environmental pressure, low energy consumption, low production cost, high purity and yields of nitrile products, and the like, and can be used for obtaining nitrile with a more complex structure. The invention also relates to a method for preparing corresponding amine with nitrile.