917-61-3

Basic information

• Product Name: Sodium cyanate
• Synonyms: sodium isocyanate;SODIUM CYANATE;Sodium cyanate ,90%;Strawberry Acid;Cyanic acid, sodiuMsalt (1:1);Sodium isocyanate Zassol;cyansan;san-cyan
• CAS NO: 917-61-3
• Molecular Formula: CNO*Na
• Molecular Weight: 65.01
• EINECS: 213-030-6
• Product Categories: Catalysis and Inorganic Chemistry;Chemical Synthesis
• Mol File: 917-61-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 550 °C
• Boiling Point: 23.5 °C at 760 mmHg
• Appearance: White to light yellow or light beige/Crystalline Powder and/Chunks
• Density: 1,937 g/cm3
• Vapor Pressure: 6750mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Water (Slightly)
• Water Solubility: 110 g/L (20 ºC)
• Stability: Stable. Incompatible with acids, strong oxidizing agents.
• Merck: 14,8604
• BRN: 3594963
• CAS DataBase Reference: Sodium cyanate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium cyanate(917-61-3)
• EPA Substance Registry System: Sodium cyanate(917-61-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22-52/53
• Safety Statements: 24/25-61
• WGK Germany: 1
• RTECS: GS7000000
• TSCA: Yes
• Hazardous Substances Data: 917-61-3(Hazardous Substances Data)

Usage

Description

Sodium cyanate belongs to the sodium salt of cyanic acid, which is commonly applied in the fields of chemical industry and medicine. Its industrial application is to serve as an intermediate in the production of dye-stuffs, bulk drug, heat treatment salts for metals, fungicides, herbicides, and photographic initiators. It is also an ideal nucleophile. The nucleophile properties of sodium cyanate makes it a major contributor to the stereospecificity in certain reactions such as in the production of chiral oxazolidone. Besides, it also acts as a reagent in the production of asymmetrical urea which have a range of biological activity mostly in aryl isocyanate intermediates. These intermediates and sodium cyanate have been applied in medicine, displaying counterbalancing carcinogenic effects on human body, which is probably effective with sickle cell anemia and helpful to block certain receptors for melanin which has been indicated to be helpful with obesity.

References

https://en.wikipedia.org/wiki/Sodium_cyanate http://www.recentlab.com/sodiumcyanate.htm http://www.jfine.co.jp/eng/chemicals/use/cyanate/index.html

Uses

Different sources of media describe the Uses of 917-61-3 differently. You can refer to the following data:
1. Organic synthesis, heat treating of steel, inter- mediate for manufacture of medicinals.
2. Sodium Cyanate is used in biological study as tumor cell proliferation and metabolism inhibition.

Flammability and Explosibility

Nonflammable

Safety Profile

Poison by ingestion, intraperitoneal, and intramuscular routes. Human systemic effects by ingestion: weight loss, changes in the visual field, and other eye effects. See also CYANATES. When heated to decomposition it emits very toxic fumes of CNand Na2O.

Purification Methods

It forms colourless needles from EtOH. Its solubility in EtOH is 0.22g/100g at 0oC. It is soluble in H2O but can be recrystallised from small volumes of it.

InChI:InChI=1/CNO.Na/c2-1-3;/q-1;+1

Synthetic route

[NaNV(N(3,5-Me2C6H3)(t-Bu))3]2 complex + carbon monoxide (201230-82-2) → V(N(3,5-Me2C6H3)(t-Bu))3 + sodium isocyanate (917-61-3)

Conditions	Yield
In tetrahydrofuran 1 atm of CO, THF, 23°C, 24 h; extd. with hexane, filtered, concd., the filtrate was stored at -35°C;	A 71% B 77%

sodium carbonate (497-19-8) + urea (57-13-6) → sodium isocyanate (917-61-3) + sodium allophanate (26597-39-7)

Conditions	Yield
at 140℃; for 2h; Product distribution; Thermodynamic data; var. time, var. temp., activation energy;	A 66.1% B 15.2%

ammonium cyanate (22981-32-4) + sodium hydroxide (1310-73-2) → sodium isocyanate (917-61-3)

Conditions	Yield
In ethanol react. of soln. of NaOH and NH4OCN (suspn., excess) at 10°C; pptn.;; washing with ethanol, then with ether;;	61%
In ethanol react. of soln. of NaOH and NH4OCN (suspn., excess) at 10°C; pptn.;; washing with ethanol, then with ether;;	61%

carbamic acid-(3-chloro-propyl ester) (6326-12-1) + sodium ethanolate (141-52-6) → sodium isocyanate (917-61-3)

Conditions	Yield
With sodium hypochlorite
With sodium hypochlorite

sodium methylate (124-41-4) + urea (57-13-6) → sodium isocyanate (917-61-3)

Conditions	Yield
In methanol byproducts: NH3; boiling soln. of educts at 105°C under pressure and reflux; evapn. of NH3 by an outlet;; low Na2CO3 content;;
In methanol byproducts: NH3; heating CH3ONa soln. and dried urea with stirring up to boiling; heating at 120°C, 2-3h;; impurity 0.5-1.5% Na2CO3;;
With methanol at 105℃;
In methanol byproducts: NH3; boiling soln. of educts at 105°C under pressure and reflux; evapn. of NH3 by an outlet;; low Na2CO3 content;;
In methanol byproducts: NH3; heating CH3ONa soln. and dried urea with stirring up to boiling; heating at 120°C, 2-3h;; impurity 0.5-1.5% Na2CO3;;

urea (57-13-6) → sodium isocyanate (917-61-3)

Conditions	Yield
With sodium hydroxide; potassium nitrate at 89.9℃; Rate constant; Thermodynamic data; Mechanism; ΔG(excit.), ΔH(excit.), ΔS(excit.), Ea, var. pH;
With sodium nitrite at 530℃;
With sodium hypobromide
With sodium amalgam In neat (no solvent) strongly mixing educts at 140-200°C;;
With sodium; toluene at 110℃; und Erhitzen des vom Toluol befreiten Reaktionsgemisches auf 165grad;

urethane → sodium isocyanate (917-61-3)

Conditions	Yield
With sodium; benzene

carbamate sodium → sodium isocyanate (917-61-3)

Conditions	Yield
beim Gluehen;

calcium cyanamide (156-62-7) + Na2CO3 → sodium isocyanate (917-61-3)

Conditions	Yield
at 500℃;
at 500℃;

urea (57-13-6) + NaH → sodium isocyanate (917-61-3)

Conditions	Yield
at 140℃;
at 140℃;

urea (57-13-6) + NaNH2 → sodium isocyanate (917-61-3)

Conditions	Yield
at 140℃;
at 140℃;

NH3 + CO2 → sodium isocyanate (917-61-3)

Conditions	Yield
With carbon monoxide at 650℃; in Schmelzen aus Natriumcyanat und Na2S oder Na2CO3;
at 650℃; in Schmelzen aus Natriumcyanat und Na2S oder Na2CO3;

sodium carbonate → sodium isocyanate (917-61-3)

Conditions	Yield
With ammonia bei Dunkelrotglut;
With ammonia bei Dunkelrotglut;

urea (57-13-6) + sodium carbonate → sodium isocyanate (917-61-3)

CO2 + NH3 + sodium carbonate → sodium isocyanate (917-61-3)

Conditions	Yield
With copper at 650℃;

urea (57-13-6) + sodium hydrogencarbonate → sodium isocyanate (917-61-3)

CO2 + NH3

Conditions	Yield
With magnesium oxide at 650℃;

Upstream product

• 6326-12-1 carbamic acid-(3-chloro-propyl ester) 
• 141-52-6 sodium ethanolate 
• 57-13-6 urea 
• 201230-82-2 carbon monoxide 
• 1101192-00-0 V(NCO)(N(C(CH₃)3)C₆H₃(CH₃)2)3 
• 460-19-5 ethanedinitrile 
• 7757-83-7 sodium sulfite 
• 1313-82-2 sodium sulfide 
• 156-62-7 calcium cyanamide 
• 497-19-8 sodium carbonate 
• 7632-00-0 sodium nitrite 
• 592-04-1 mercury(II) cyanide 
• 506-64-9 silver(I) cyanide 
• 51-79-6 urethane 

Downstream Products

• 108-80-5 isocyanuric acid 
• 36384-97-1 Diisocyanato-phenylthiophosphonsaeure 
• 32847-52-2 2-isocyanato-3-phenyl-[1,3,2]oxazaphospholidine 
• 92029-20-4 2,6-Dioxo-4-phenyl-cyclohexanecarboxylic acid amide 
• 79996-68-2 (E)-3,5-hexadienyl carbamate 
• 78-44-4 carisoprodol 
• 86576-00-3 1-(m-chlorophenyl)-1-phenylurea 
• 129966-10-5 (S)-trans-2-phenylcyclohexyl carbamate 
• 84418-43-9 9-fluorenylmethyl carbamate 
• 155883-52-6 1-carbamoylindoline-2-carboxylic acid 
• 53544-67-5 2-carboxamidocyclohexane-1,3-dione 
• 140-38-5 N-(4-chlorophenyl)urea 
• 38765-81-0 trans-1-iodo-2-isocyanatocyclohexane 
• 192570-28-8 2-ureido-6-chlorobenzoic acid 

Relevant articles and documents

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CROSS-LINKED COMPOSITIONS

Improved compositions comprising a cross-linkable protein or polypeptide, and a non-toxic material which induces cross-linking of the cross-linkable protein. The compositions are optionally and preferably prepared in a non-phosphate buffer solvent. Optionally and preferably, the cross-linkable protein includes gelatin and any gelatin variant or variant protein as described herein. Optionally and preferably, the non-toxic material comprises transglutaminase (TG), which may optionally comprise any type of calcium dependent or independent transglutaminase, which may for example optionally be a microbial transglutaminase (mTG).

Kinetics and mechanism of alkaline hydrolysis of urea and sodium cyanate

The kinetics of hydrolysis of urea has been studied in 0.5 to 3.0 mol dm-3 sodium hydroxide solution at different temperatures. Urea hydrolysis follows an irreversible first order consecutive reaction path: equation presented The variation of Klobs with [alkali] is linear at [OH-] = 5.0 to 1.5 mol dm-3, thereafter a sharp increase in the reaction rate is observed for first step hydrolysis of urea. The second step rate constant (K2obs) is found to be independent of [alkali]. Hydrolysis of urea in alkaline medium follows an elemination-addition mechanism. The reaction does not proceed through the formation and decomposition of tetrahedral intermediate. Sodium cyanate hydrolysis obeys an irreversible pseudo-first order kinetics. [OH-] has no significant effect on the rate constants. The following rate equations have been derived for the two step hydrolysis of urea. Klobs = K0 + K1[OH-](K4 + K3[OH-])/K-1 + K4 + K3[OH-] K2obs = K2Kh On the basis of observed data, probable mechanisms have been proposed.